545. The New Rules of Buying Short-Term Rentals in 2026

In this episode of Thanks for Visiting, hosts Sarah Karakayan and Annette Grant welcome back Kenny Bedwell, CEO of the top STR deal-finding platform and a five-time STR investor, to discuss the evolving landscape of short-term rental investments in 2026. Kenny shares his data-driven strategy for success, emphasizing the importance of targeting early-adopter markets—like Kentucky’s Bourbon Trail—where demand is strong but competition is still manageable. He reveals how he transformed a $1M property into the top-performing STR in the state, grossing $425K in revenue by niche-targeting older groups with tailored amenities like hot tubs, a golf simulator, and a fish pond. The episode underscores a critical shift: short-term rentals are no longer passive income. With supply doubling over the past three years and average revenue dropping 10% annually, only the top 10% of properties are thriving. Kenny warns against copying successful models without considering cost, debt, and market timing, advocating instead for strategic diversification across platforms like VRBO and direct booking to stay competitive. The hosts and Kenny stress that the future belongs to professionalized operators who invest in design, revenue management, and guest experience. They highlight that guest expectations have risen dramatically—properties must now meet 2026 standards with modern appliances, intentional design, and consistent operations. Kenny also reveals his pivot toward boutique hotel investing for long-term wealth building, as hotels can be appraised based on income, enabling greater appreciation and equity growth. The episode concludes with a powerful message: success in 2026 requires active management, innovation, and a mindset shift from passive ownership to professional operation. For aspiring investors, Kenny’s advice is clear: don’t chase trends—find underserved markets, understand your guest avatar, and build a unique, high-performing asset.